Acrylic acid derivative-containing composition, and method for stabilizing acrylic acid derivative

ABSTRACT

An object of the present invention is to provide a method for stabilizing an acrylic acid derivative, and a composition containing an acrylic acid derivative in which the acrylic acid derivative is stabilized. The present invention provides a composition comprising: (A) an acrylic acid derivative represented by Formula (I): 
                         
(wherein R 1  and R 2  are the same or different, and each represents alkyl, fluoroalkyl, aryl that may have one or more substituents, halogen, or hydrogen; R 3  represents alkyl, fluoroalkyl, aryl that may have one or more substituents, or hydrogen; and X represents fluoroalkyl, alkyl, halogen, or hydrogen); and (B) alcohol, wherein the content of acrylic acid derivative (A) is 30% (w/w) or more.

TECHNICAL FIELD

The present invention relates to a composition containing an acrylicacid derivative, a method for stabilizing an acrylic acid derivative,and the like.

BACKGROUND ART

Acrylic acid derivatives are widely used for (1) materials ofwater-absorbing polymers, (2) materials of acrylic resins as asubstitute for inorganic glass for use in window materials for buildingsand vehicles, coverings for lighting equipment, lantern signs, roadsigns, daily necessities, office supplies, crafts, windscreens ofwatches, and the like, and (3) acrylic resin coating materials. Amongacrylic acid derivatives, fluorine-containing acrylic acid derivativesare useful as synthetic intermediates of pharmaceuticals (e.g.,antibiotics), synthetic intermediates for sheath materials of opticalfibers, synthetic intermediates of coating materials, syntheticintermediates of semiconductor resist materials, and monomers offunctional polymers.

Examples of known methods for producing an acrylic acid derivativeinclude a method of producing an acrylic acid derivative by oxidizingisobutylene or propylene, and a method of producing an acrylic acidderivative using ethylene, propyne, or the like as a starting materialusing a transition metal catalyst.

Further, as examples of methods for producing a fluorine-containingacrylic acid derivative, for example, Patent Document 1 discloses amethod of reacting a 2-fluoropropionic ester with anitrogen-bromine-bond-containing brominating agent in the presence of aradical initiator, and Patent Document 2 discloses a process forconverting a 3-halo-2-fluoropropionic acid derivative to a substituted2-fluoroacrylic acid derivative in the presence of at least one kind ofbase and at least one kind of polymerization inhibitor.

CITATION LIST Patent Documents

-   Patent Document 1: JP2011-001340A-   Patent Document 2: JP2012-530756A

SUMMARY OF INVENTION Technical Problem

Since an acrylic acid derivative contains an active unsaturated bond dueto its structure, it is unstable against external stimuli such as heat,light, and oxygen, and may easily change into an oligomer or a polymerby a polymerization reaction or the like.

Therefore, a method for stabilizing an acrylic acid derivative, and acomposition comprising an acrylic acid derivative in which the acrylicacid derivative is stabilized, have been in demand.

An object of the present invention is to provide a method forstabilizing an acrylic acid derivative, and a composition comprising anacrylic acid derivative in which the acrylic acid derivative isstabilized.

Solution to Problem

The inventors of the present invention conducted extensive research andfound that the above problem can be solved by a composition comprising:

(A) an acrylic acid derivative represented by Formula (I):

(wherein R¹ and R² are the same or different, and each represents alkyl,fluoroalkyl, aryl that may have one or more substituents, halogen, orhydrogen; R³ represents alkyl, fluoroalkyl, aryl that may have one ormore substituents, or hydrogen; and X represents fluoroalkyl, alkyl,halogen, or hydrogen); and

(B) alcohol.

With this finding, the inventors completed the present invention.

The present invention includes the following aspects.

Item 1.

A composition comprising:

(A) an acrylic acid derivative represented by Formula (I):

(wherein R¹ and R² are the same or different, and each represents alkyl,fluoroalkyl, aryl that may have one or more substituents, halogen, orhydrogen; R³ represents alkyl, fluoroalkyl, aryl that may have one ormore substituents, or hydrogen; and X represents fluoroalkyl, alkyl,halogen, or hydrogen); and

(B) alcohol,

wherein the content of acrylic acid derivative (A) is 30% (w/w) or more.

Item 2.

The composition according to Item 1, wherein alcohol (B) is C₁₋₆alcohol.

Item 3.

The composition according to Item 2, wherein alcohol (B) is methanol.

Item 4.

The composition according to any one of Items 1 to 3, wherein R¹ ishydrogen, C₁₋₂₀ alkyl, or C₁₋₂₀ fluoroalkyl.

Item 5.

The composition according to any one of Items 1 to 4, wherein R¹ ishydrogen.

Item 6.

The composition according to any one of Items 1 to 5, wherein R² ishydrogen, C₁₋₂₀ alkyl, or C₁₋₂₀ fluoroalkyl.

Item 7.

The composition according to any one of Items 1 to 6, wherein R² ishydrogen.

Item 8.

The composition according to any one of Items 1 to 7, wherein R³ isC₁₋₂₀ linear alkyl.

Item 9.

The composition according to any one of Items 1 to 8, wherein X is C₁₋₂₀fluoroalkyl, fluorine, or chlorine.

Item 10.

The composition according to any one of Items 1 to 9, wherein X isfluorine.

Item 11.

A method for stabilizing an acrylic acid derivative represented byFormula (I):

(wherein R¹ and R² are the same or different, and each represents alkyl,fluoroalkyl, aryl that may have one or more substituents, halogen, orhydrogen; R³ represents alkyl, fluoroalkyl, aryl that may have one ormore substituents, or hydrogen; and X represents fluoroalkyl, alkyl,halogen, or hydrogen),

the method comprising making the acrylic acid derivative represented byFormula (I) coexist with alcohol.

Advantageous Effects of Invention

The composition of the present invention contains an acrylic acidderivative; in the composition, the acrylic acid derivative isstabilized.

The method of the present invention stabilizes an acrylic acidderivative.

DESCRIPTION OF EMBODIMENTS Terms

The symbols and the abbreviations in this specification are to beinterpreted as having the general meanings in the related technicalfield to which the present invention pertains, according to the contextof this specification, unless otherwise specified.

In this specification, the term “comprise/contain” is intended to meanboth “consist essentially of” and “consist of.”

In this specification, “stabilization” of an acrylic acid derivativerefers to preventing an acrylic acid derivative from changing into adifferent substance, such as a polymer.

In this specification, “alkyl” (the term “alkyl” encompasses the “alkyl”moiety in “fluoroalkyl” or the like) may be a cyclic, linear, orbranched alkyl.

In this specification, “alkyl” may be, for example, a C₁₋₂₀, C₁₋₁₂,C₁₋₆, C₁₋₄, or C₁₋₃ alkyl.

In this specification, specific examples of “alkyl” include methyl,ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl,pentyl, neopentyl, hexyl, and like linear or branched alkyl.

In this specification, specific examples of “alkyl” include cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl and like C₃₋₆ cyclic alkyl(cycloalkyl).

In this specification, “fluoroalkyl” refers to an alkyl in which atleast one hydrogen is replaced by fluorine.

In this specification, the number of fluorines in the “fluoroalkyl” maybe one or more (the maximum replaceable number from 1; e.g., 1 to 3, 1to 6, or 1 to 12).

The “fluoroalkyl” encompasses perfluoroalkyl. The “perfluoroalkyl”refers to an alkyl in which all of the hydrogens are replaced byfluorines.

In this specification, examples of “fluoroalkyl” include C₁₋₂₀, C₁₋₁₂,C₁₋₆, C₁₋₄, and C₁₋₃ fluoroalkyls.

In this specification, the “fluoroalkyl” may be a linear or branchedfluoroalkyl.

In this specification, specific examples of “fluoroalkyl” includefluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl,pentafluoroethyl, tetrafluoropropyl (e.g., HCF₂CF₂CH₂—),hexafluoropropyl (e.g., (CF₃)₂CH—), nonafluorobutyl, octafluoropentyl(e.g., HCF₂CF₂CF₂CF₂CH₂—), and tridecafluorohexyl.

In this specification, examples of “aryl” include phenyl and naphthyl.

In this specification, examples of “halogen” include fluorine, chlorine,bromine, and iodine.

In this specification, the “alkoxy” is an alkyl-O-group.

In this specification, examples of “acyl” include alkanoyl (i.e.,alkyl-CO-group).

In this specification, examples of “ester” include alkylcarbonyloxy(i.e., alkyl-CO—O-group), and alkoxycarbonyl (i.e., alkyl-O—CO-group).

Composition

The composition of the present invention comprises:

(A) an acrylic acid derivative represented by Formula (I):

(wherein R¹ and R² are the same or different, and each represents alkyl,fluoroalkyl, aryl that may have one or more substituents, halogen, orhydrogen; R³ represents alkyl, fluoroalkyl, aryl that may have one ormore substituents, or hydrogen; and X represents fluoroalkyl, alkyl,halogen, or hydrogen]) (in this specification, this derivative may alsobe referred to as “acrylic acid derivative (A)”); and

(B) alcohol,

wherein the content of acrylic acid derivative (A) is 30% (w/w) or more.

Acrylic Acid Derivative (A)

Each symbol in Formula (1) representing acrylic acid derivative (A) isexplained below.

Preferable examples of the substituents of the “aryl that may have oneor more substituents” represented by R¹, R², and R³ include fluorine,alkyl, alkoxy, acyl, ester, cyano, nitro, and fluoroalkyl. Morepreferable examples include fluorine.

The number of “the substituents” is preferably 0 (i.e., unsubstituted),1, 2, or 3.

R¹ is preferably hydrogen, C₁₋₂₀ (preferably C₁₋₁₂, more preferablyC₁₋₆, further preferably C₁₋₄, further more preferably C₁₋₃,particularly preferably C₁ or C₂) alkyl, or C₁₋₂₀ fluoroalkyl, and morepreferably hydrogen.

R² is preferably hydrogen, C₁₋₂₀ (preferably C₁₋₁₂, more preferablyC₁₋₆, further preferably C₁₋₄, further more preferably C₁₋₃,particularly preferably C₁ or C₂) alkyl, or C₁₋₂₀ (preferably C₁₋₁₂,more preferably C₁₋₆, further preferably C₁₋₄, further more preferablyC₁₋₃, particularly preferably C₁ or C₂) fluoroalkyl, and more preferablyhydrogen.

R³ is preferably C₁₋₂₀ (preferably C₁₋₁₂, more preferably C₁₋₆, furtherpreferably C₁₋₄, further more preferably C₁₋₃, particularly preferablyC₁ or C₂) linear alkyl.

X is C₁₋₂₀ (preferably C₁₋₁₂, more preferably C₁₋₆, further preferablyC₁₋₄, further more preferably C₁₋₃, particularly preferably C₁ or C₂)fluoroalkyl, fluorine, or chlorine, and more preferably fluorine.

In Formula (I), preferably,

R¹ is hydrogen,

R² is hydrogen,

R³ is methyl or ethyl (more preferably methyl), and

X is fluorine or chlorine (more preferably fluorine).

The composition of the present invention may comprise one or more kindsof acrylic acid derivative (A); however, the composition of the presentinvention preferably comprises only one kind of acrylic acid derivative(A).

Acrylic acid derivative (A) used in the present invention may beproduced by a known method or a similar method thereof, or may beobtained from commercial suppliers.

Acrylic acid derivative (A) used in the present invention may beproduced, for example, through the production methods disclosed inInternational Publication No. 2014/034906, JP2014-24755A, U.S. Pat. No.3,262,968, and the like, or similar methods thereof.

The content of acrylic acid derivative (A) in the composition of thepresent invention is 30% (w/w) or more.

Generally, when the concentration of acrylic acid derivative (A) ishigh, unintended polymerization reaction or the like more easily occurs.However, in the composition of the present invention, even when thecontent of acrylic acid derivative (A) is high, acrylic acid derivative(A) is stable.

Further, the content of acrylic acid derivative (A) in the compositionof the present invention is preferably 35% (w/w) or more, 40% (w/w) ormore, 50% (w/w) or more, 60% (w/w) or more, 70% (w/w) or more, 80% (w/w)or more, or 90% (w/w) or more.

Further, the content of acrylic acid derivative (A) in the compositionof the present invention is preferably 30 to 90% (w/w), 30 to 80% (w/w),35 to 70% (w/w), or 35 to 65% (w/w).

The upper limit of the content of acrylic acid derivative (A) in thecomposition of the present invention is, for example, but notparticularly limited to, 98% (w/w), 95% (w/w), 90% (w/w), 80% (w/w), 70%(w/w), or 65% (w/w). However, as it would be obvious to a person skilledin the art, the upper limit of the content of acrylic acid derivative(A) in the composition of the present invention may be limited dependingon the amount of alcohol (B) contained in the composition of the presentinvention.

Alcohol (B)

Alcohol (B) contained in the composition of the present invention ispreferably C₁₋₆ alcohol.

Examples of alcohol (B) contained in the composition of the presentinvention include methanol, ethanol, n-propanol, isopropanol, n-butanol,isobutanol, tert-butanol, pentanol, and hexanol.

Alcohol (B) contained in the composition of the present invention isparticularly preferably methanol.

In the present invention, alcohol (B) may be a single kind or acombination of two or more kinds of alcohol (B).

The lower limit of the content of alcohol (B) in the composition of thepresent invention is preferably 0.02% (w/w), more preferably 0.03%(w/w), further preferably 0.1% (w/w), further more preferably, 0.3%(w/w), particularly preferably 0.5% (w/w), and particularly preferably1% (w/w), 1.5% (w/w), 2.0% (w/w), particularly preferably 3.0%, moreparticularly preferably 5.0% (w/w).

In accomplishing the stabilization of acrylic acid derivative (A), inthe composition of the present invention, the upper limit of the contentof alcohol (B) is not particularly limited; however, using alcohol (B)in an amount more than the amount ensuring the desired stabilization ofacrylic acid derivative (A) is a disadvantage in terms of cost.Therefore, the upper limit of the content of alcohol (B) in thecomposition of the present invention is generally, for example, 70%(w/w), 50% (w/w), 40% (w/w), 30% (w/w), 20% (w/w), 15% (w/w), 10% (w/w),7% (w/w), 6% (w/w), 5% (w/w), 4% (w/w), or 3% (w/w).

The content of alcohol (B) in the composition of the present inventionis preferably 0.01 to 70% (w/w), 0.01 to 50% (w/w), or in a range of0.02 to 6% (w/w), more preferably in a range of 0.03 to 5% (w/w),further preferably in a range of 0.1 to 4% (w/w), further morepreferably in a range of 0.3 to 3.5 (w/w), particularly preferably 0.5to 3% (w/w), and further particularly preferably in a range of 1 to 3%(w/w).

In the composition of the present invention, the lower limit of theratio of alcohol (B) to acrylic acid derivative (A) [alcohol (B)/acrylicacid derivative (A)] is preferably 0.02% (w/w), more preferably 0.03%(w/w), further preferably 0.1% (w/w), further more preferably 0.3%(w/w), particularly preferably 0.5% (w/w), and particularly preferably1% (w/w).

In accomplishing the stabilization of acrylic acid derivative (A), theupper limit of the ratio of alcohol (B) to acrylic acid derivative (A)[alcohol (B)/acrylic acid derivative (A)] is not particularly limited;however, using alcohol (B) in an amount more than the amount ensuringthe desired stabilization of acrylic acid derivative (A) is adisadvantage in terms of cost. Therefore, the upper limit of the ratioof alcohol (B) to acrylic acid derivative (A) [alcohol (B)/acrylic acidderivative (A)] is generally, for example, 200% (w/w), 190% (w/w), 170%(w/w), 150% (w/w), 100% (w/w), 70% (w/w), 50% (w/w), 40% (w/w), 30%(w/w), 20% (w/w), 15% (w/w), 10% (w/w), 7% (w/w), 6% (w/w), 5% (w/w), 4%(w/w), or 3% (w/w).

In the composition of the present invention, the ratio of alcohol (B) toacrylic acid derivative (A) is preferably 0.01 to 200% (w/w), 0.01 to190% (w/w), 0.01 to 170% (w/w), 0.01 to 100% (w/w), or in a range of0.02 to 6% (w/w), more preferably in a range of 0.03 to 5% (w/w),further preferably in a range of 0.1 to 4% (w/w), further morepreferably in a range of 0.3 to 3.5 (w/w), particularly preferably 0.5to 3% (w/w), and particularly preferably in a range of 1 to 3% (w/w).

Optional Components

The composition of the present invention may contain optional componentsin addition to acrylic acid derivative (A) and alcohol (B). The optionalcomponents may be impurities that coexist with acrylic acid derivative(A) or alcohol (B) prepared for the production of the composition of thepresent invention.

Examples of the optional components include water and organic solvents.

In the composition of the present invention, since acrylic acidderivative (A) is stabilized by alcohol (B), the significance of using apolymerization inhibitor for the purpose of stabilizing acrylic acidderivative (A) is small; however, the composition of the presentinvention may contain a polymerization inhibitor as an optionalcomponent.

As a method for preventing unintended polymerization reaction or thelike, a method of using a polymerization inhibitor, such as thepolymerization inhibitor disclosed in Patent Document 2, has been known.However, acrylic acid derivative (A) may be exposed to variousconditions, for example, upon storage or at the time of use. Since theboiling points of versatile polymerization inhibitors greatly differfrom that of an acrylic acid derivative, it is often difficult to makethem coexist with an acrylic acid derivative. In this case, thepolymerization inhibitors cannot fully exhibit its function.

Stability of the Composition of the Present Invention

In the composition of the present invention, acrylic acid derivative (A)is stabilized. More specifically, acrylic acid derivative (A) containedin the composition of the present invention has high stability.

Specifically, for example, acrylic acid derivative (A) in thecomposition of the present invention is prevented from changing into apolymer or the like, compared with a case in which acrylic acidderivative (A) does not coexist with alcohol (B).

In the present invention, the change of acrylic acid derivative (A) intoa different substance may be analyzed, for example, using NMR analysisor the like. Further, for example, the change of acrylic acid derivativeinto a polymer may be easily detected by observation of a change of acolorless transparent solution of acrylic acid derivative into a solid,or the like.

In the composition of the present invention, acrylic acid derivative (A)is stabilized by the coexistence with alcohol (B).

A method for making the acrylic acid derivative coexist with apolymerization inhibitor has been known as a means for stabilizing anacrylic acid derivative.

However, since acrylic acid derivative (A) may be exposed to variousconditions, for example, upon storage or at the time of use, thecoexistence of a polymerization inhibitor with an acrylic acidderivative may be difficult in some cases. In this case, thepolymerization inhibitor cannot fully exhibit its function.

In contrast, since alcohol (B) may have a boiling point similar to thatof acrylic acid derivative (A), it is easy to make alcohol (B) coexistwith acrylic acid derivative (A). Therefore, acrylic acid derivative (A)in the composition of the present invention is stable under variousconditions.

In addition, when acrylic acid derivative (A) in the composition of thepresent invention is subjected to a polymerization reaction or the like,optionally, the reactivity of acrylic acid derivative (A) can beincreased by removing alcohol (B) by a usual method such as washing withwater.

Production Method

The composition of the present invention may be produced by mixingacrylic acid derivative (A), alcohol (B), and optional components using,for example, a usual method such as stirring.

Some or all of alcohol (B) may be contained as an impurity or anadditive in acrylic acid derivative (A) prepared for the production ofthe composition of the present invention.

Method for Stabilizing Acrylic Acid Derivative (A)

The method for stabilizing the acrylic acid derivative (acrylic acidderivative (A)) represented by Formula (I) of the present inventioncomprises making acrylic acid derivative (A) coexist with alcohol(alcohol (B)).

The method for making acrylic acid derivative (A) coexist with alcohol(B) is not particularly limited. Examples of the method include:

[1] a method of mixing acrylic acid derivative (A) and alcohol (B);

[2] a method of producing alcohol (B) in a system containing acrylicacid derivative (A);

[3] a method of producing acrylic acid derivative (A) in a systemcontaining alcohol (B); and

[4] a method of individually producing acrylic acid derivative (A) andalcohol (B) in a single system.

The same explanation of acrylic acid derivative (A) as that regardingthe composition of the present invention can be applied to acrylic acidderivative (A) used in the method for stabilizing acrylic acidderivative (A) of the present invention.

The same explanation of alcohol (B) as that regarding the composition ofthe present invention can be applied to alcohol (B) used in the methodfor stabilizing acrylic acid derivative (A) of the present invention.

In the method for stabilizing acrylic acid derivative (A) of the presentinvention, preferably, alcohol (B) is used at a predetermined ratiorelative to acrylic acid derivative (A). The ratio is as described aboveregarding the composition of the present invention.

The details of the method for stabilizing acrylic acid derivative (A)including the above matters can be understood from the above explanationregarding the composition of the present invention.

EXAMPLES

The present invention is described below in more detail with referenceto Examples. However, the present invention is not limited to theseExamples.

Compositions having the formulations shown in Table 1 were prepared. Thecompositions were colorless and transparent liquids.

Each composition was placed in a container, which was closed with astopper. Stirring was performed for an hour at an outside temperature of65° C., and generation of a solid was visually confirmed, therebyconfirming whether a polymer was generated.

Generation of polymer was not confirmed in Composition a, b, c, d, or e.

In contrast, in Comparative Example 1 performed under the sameconditions (methanol was not added), generation of polymer wasconfirmed.

Composition f was placed in a container, which was closed with astopper. Stirring was performed for 30 minutes at an outside temperatureof 40° C., and generation of a solid was visually confirmed, therebyconfirming whether a polymer was generated.

Generation of polymer was not confirmed in composition f.

In contrast, in Comparative Example 2 performed under the sameconditions (methanol was not added), generation of polymer wasconfirmed.

TABLE 1 2-Fluoroacrylic Acid Composition MeOH Methyl Ester a 2.4% (w/w)97.6% (w/w) b 2.0% (w/w) 98.0% (w/w) c 2.3% (w/w) 97.7% (w/w) d 5.1%(w/w) 94.9% (w/w) e 0.3% (w/w) 99.7% (w/w) Comparative Not added  100%(w/w) Example 1 f 0.02% (w/w)  99.98% (w/w)  Comparative Not added  100%(w/w) Example 2

Example g

2-fluoroacrylic acid methyl ester purified by distillation as an acrylicacid derivative and methyl alcohol at a weight ratio of 35:65 wereplaced in a 10-mL test tube. The test tube was closed with a stopper andmixing was performed, thereby preparing a sample. Regarding theappearance and the characteristics of the composition sample immediatelyafter the preparation, the composition sample was a colorless andtransparent liquid.

The test tube containing the sample was allowed to stand at 40° C., andthe appearance and the characteristics of the sample were confirmedafter six hours; the composition sample was a colorless and transparentliquid.

Example h

2-fluoroacrylic acid methyl ester purified by distillation as an acrylicacid derivative and methyl alcohol at a weight ratio of 60:40 wereplaced in a 10-mL test tube. The test tube was closed with a stopper andmixing was performed, thereby preparing a sample. Regarding theappearance and the characteristics of the composition sample immediatelyafter the preparation, the composition sample was a colorless andtransparent liquid.

The test tube containing the sample was allowed to stand at 40° C., andthe appearance and the characteristics of the sample were confirmedafter six hours; the composition sample was a colorless and transparentliquid.

Example i

2-fluoroacrylic acid methyl ester purified by distillation as an acrylicacid derivative and methyl alcohol at a weight ratio of 35:65 wereplaced in a 10-mL test tube. The test tube was closed with a stopper andmixing was performed, thereby preparing a sample. Regarding theappearance and the characteristics of the composition sample immediatelyafter the preparation, the composition sample was a colorless andtransparent liquid.

The test tube containing the sample was allowed to stand at 65° C., andthe appearance and the characteristics of the sample were confirmedafter six hours; the composition sample was a colorless and transparentliquid.

Example j

2-fluoroacrylic acid methyl ester purified by distillation as an acrylicacid derivative and methyl alcohol at a weight ratio of 60:40 wereplaced in a 10 mL test tube. The test tube was closed with a stopper andmixing was performed, thereby preparing a sample. Regarding theappearance and the characteristics of the composition sample immediatelyafter the preparation, the composition sample was a colorless andtransparent liquid.

The test tube containing the sample was allowed to stand at 65° C., andthe appearance and the characteristics of the sample were confirmedafter six hours; the composition sample was a colorless and transparentliquid.

The invention claimed is:
 1. A composition comprising: (A) an acrylicacid derivative represented by Formula (I):

wherein R¹ and R² are the same or different, and each represents alkyl,fluoroalkyl, aryl that may have one or more substituents, halogen, orhydrogen; R³ represents alkyl, fluoroalkyl, aryl that may have one ormore substituents, or hydrogen; and X is C₁₋₂₀ fluoroalkyl, fluorine, orchlorine; and (B) alcohol, wherein the content of acrylic acidderivative (A) is 30% (w/w) or more.
 2. The composition according toclaim 1, wherein alcohol (B) is C₁₋₆ alcohol.
 3. The compositionaccording to claim 2, wherein alcohol (B) is methanol.
 4. Thecomposition according to claim 1, wherein R¹ is hydrogen, C₁₋₂₀ alkyl,or C₁₋₂₀ fluoroalkyl.
 5. The composition according to claim 1, whereinR¹ is hydrogen.
 6. The composition according to claim 1, wherein R² ishydrogen, C₁₋₂₀ alkyl, or C₁₋₂₀ fluoroalkyl.
 7. The compositionaccording to claim 1, wherein R² is hydrogen.
 8. The compositionaccording to claim 1, wherein R³ is C₁₋₂₀ linear alkyl.
 9. Thecomposition according to claim 1, wherein X is fluorine.
 10. A methodfor stabilizing (A) an acrylic acid derivative represented by Formula(I):

wherein R¹ and R² are the same or different, and each represents alkyl,fluoroalkyl, aryl that may have one or more substituents, halogen, orhydrogen; R³ represents alkyl, fluoroalkyl, aryl that may have one ormore substituents, or hydrogen; and X represents fluoroalkyl, alkyl,halogen, or hydrogen, the method comprising making the acrylic acidderivative represented by Formula (I) coexist with alcohol.